Chiral Phosphoric Acid-Catalyzed Enantioselective Construction of 2,3-Disubstituted Indolines
Wei‐Yang Ma, Coralie Gelis, Damien Bouchet, Pascal Retailleau, Xavier Moreau, Luc Neuville, Géraldine Masson
Abstract
Highly enantio- and regioselective (3 + 2) formal cycloaddition of β-substituted ene- and thioenecarbamates as well as cyclic enamides with quinone diimides catalyzed by a BINOL- and SPINOL-derived phosphoric acid is reported. A wide variety of 2,3-disubstituted 2-aminoindolines, including polycyclic ones, were prepared in generally high yields (up to 98%) with moderate to complete diastereoselectivities and in most cases excellent enantioselectivities (up to 99% ee).
Topics & Concepts
ChemistryPhosphoric acidRegioselectivityEnantioselective synthesisCycloadditionCatalysisCombinatorial chemistryOrganic chemistryAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions